#------------------------------------------------------------------------------
#$Date: 2016-03-25 09:54:20 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179735 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/31/7003157.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7003157
loop_
_publ_author_name
'Yen, Swee Kuan'
'Koh, Lip Lin'
'Huynh, Han Vinh'
'Hor, T. S. Andy'
_publ_section_title
;
 Pd(ii) complexes with mixed benzothiazolin-2-ylidene and phosphine
 ligands and their catalytic activities toward C--C coupling reactions
;
_journal_issue                   5
_journal_name_full               'Dalton Transactions'
_journal_page_first              699
_journal_page_last               706
_journal_paper_doi               10.1039/b713152f
_journal_year                    2008
_chemical_formula_sum            'C10 H16 Br N O S'
_chemical_formula_weight         278.21
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.901(2)
_cell_angle_beta                 97.785(2)
_cell_angle_gamma                112.366(2)
_cell_formula_units_Z            4
_cell_length_a                   8.7744(7)
_cell_length_b                   11.2825(9)
_cell_length_c                   13.2204(11)
_cell_measurement_reflns_used    3927
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     1182.03(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8290
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    3.624
_exptl_absorpt_correction_T_max  0.4767
_exptl_absorpt_correction_T_min  0.3553
_exptl_absorpt_correction_type   'Sadabs,(Shelrick 2001)'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_refine_diff_density_max         1.027
_refine_diff_density_min         -0.754
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         5406
_refine_ls_number_restraints     70
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0803P)²+0.5422P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1273
_reflns_number_gt                4475
_reflns_number_total             5406
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b713152f.txt
_cod_data_source_block           4298
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7003157
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.74745(4) 0.88600(3) 0.53589(3) 0.03662(12) Uani 1 1 d . . .
Br2 Br 0.69295(5) 0.14374(4) 0.19564(3) 0.04811(14) Uani 1 1 d . . .
S1 S 0.99145(14) 0.03079(9) 0.77142(7) 0.0468(2) Uani 1 1 d . . .
S2 S -0.25804(10) 0.18950(8) 0.52745(7) 0.0371(2) Uani 1 1 d . . .
N1 N 0.8436(3) 0.1305(3) 0.8829(2) 0.0376(6) Uani 1 1 d . B .
N2 N 0.0422(3) 0.3475(2) 0.5993(2) 0.0285(5) Uani 1 1 d . D .
C1 C 0.8269(5) 0.0668(3) 0.7901(3) 0.0403(8) Uani 1 1 d . . .
H1 H 0.7319 0.0436 0.7390 0.048 Uiso 1 1 calc R . .
C2 C 0.9957(4) 0.1554(3) 0.9470(2) 0.0347(7) Uani 1 1 d . . .
C3 C 1.0499(5) 0.2190(4) 1.0501(3) 0.0439(8) Uani 1 1 d . . .
H3 H 0.9834 0.2506 1.0841 0.053 Uiso 1 1 calc R . .
C4 C 1.2058(5) 0.2326(4) 1.0988(3) 0.0452(9) Uani 1 1 d . . .
H4 H 1.2455 0.2745 1.1673 0.054 Uiso 1 1 calc R . .
C5 C 1.3056(5) 0.1856(4) 1.0487(3) 0.0462(9) Uani 1 1 d . . .
H5 H 1.4107 0.1972 1.0841 0.055 Uiso 1 1 calc R . .
C6 C 1.2520(5) 0.1222(4) 0.9476(3) 0.0465(9) Uani 1 1 d . . .
H6 H 1.3183 0.0901 0.9140 0.056 Uiso 1 1 calc R . .
C7 C 1.0940(5) 0.1082(3) 0.8976(3) 0.0371(7) Uani 1 1 d . . .
C8 C 0.7174(5) 0.1770(4) 0.9137(3) 0.0562(11) Uani 1 1 d DU . .
H8A H 0.7120 0.1711 0.9859 0.067 Uiso 1 1 calc R A 1
H8B H 0.6076 0.1228 0.8723 0.067 Uiso 1 1 calc R A 1
H8C H 0.6247 0.1496 0.8554 0.067 Uiso 1 1 d R A 2
H8D H 0.6741 0.1331 0.9695 0.067 Uiso 1 1 d R A 2
C9 C 0.7661(11) 0.3199(7) 0.8975(9) 0.062(3) Uani 0.55 1 d PDU B 1
H9A H 0.8800 0.3700 0.9348 0.075 Uiso 0.55 1 calc PR B 1
H9B H 0.7676 0.3222 0.8245 0.075 Uiso 0.55 1 calc PR B 1
C10 C 0.6560(12) 0.3902(10) 0.9304(9) 0.077(3) Uani 0.55 1 d PD B 1
H10A H 0.7016 0.4780 0.9176 0.115 Uiso 0.55 1 calc PR B 1
H10B H 0.6541 0.3907 1.0028 0.115 Uiso 0.55 1 calc PR B 1
H10C H 0.5439 0.3456 0.8912 0.115 Uiso 0.55 1 calc PR B 1
C11 C -0.0517(4) 0.2249(3) 0.5569(3) 0.0324(6) Uani 1 1 d . . .
H11 H -0.0069 0.1634 0.5444 0.039 Uiso 1 1 calc R . .
C12 C -0.0513(4) 0.4229(3) 0.6096(2) 0.0279(6) Uani 1 1 d . . .
C13 C 0.0105(4) 0.5550(3) 0.6496(2) 0.0329(6) Uani 1 1 d . . .
H13 H 0.1246 0.6041 0.6734 0.039 Uiso 1 1 calc R . .
C14 C -0.1054(5) 0.6095(3) 0.6524(3) 0.0411(8) Uani 1 1 d . . .
H14 H -0.0683 0.6977 0.6781 0.049 Uiso 1 1 calc R . .
C15 C -0.2770(5) 0.5364(4) 0.6178(3) 0.0500(10) Uani 1 1 d . . .
H15 H -0.3517 0.5764 0.6214 0.060 Uiso 1 1 calc R . .
C16 C -0.3375(5) 0.4052(4) 0.5781(3) 0.0453(9) Uani 1 1 d . . .
H16 H -0.4518 0.3559 0.5557 0.054 Uiso 1 1 calc R . .
C17 C -0.2216(4) 0.3499(3) 0.5731(2) 0.0312(6) Uani 1 1 d . . .
C18 C 0.2248(4) 0.3958(4) 0.6360(3) 0.0452(9) Uani 1 1 d DU . .
H18A H 0.2807 0.4807 0.6175 0.054 Uiso 1 1 calc R C 1
H18B H 0.2679 0.3368 0.6041 0.054 Uiso 1 1 calc R C 1
H18C H 0.2702 0.3626 0.5821 0.054 Uiso 1 1 d R C 2
H18D H 0.2702 0.4896 0.6408 0.054 Uiso 1 1 d R C 2
C19 C 0.2586(9) 0.4052(8) 0.7558(6) 0.047(2) Uani 0.55 1 d PDU D 1
H19A H 0.2274 0.4729 0.7856 0.057 Uiso 0.55 1 calc PR D 1
H19B H 0.1839 0.3239 0.7722 0.057 Uiso 0.55 1 calc PR D 1
C20 C 0.4370(9) 0.4329(9) 0.8101(7) 0.063(2) Uani 0.55 1 d PDU D 1
H20A H 0.4407 0.4361 0.8833 0.094 Uiso 0.55 1 calc PR D 1
H20B H 0.5129 0.5149 0.7973 0.094 Uiso 0.55 1 calc PR D 1
H20C H 0.4693 0.3652 0.7838 0.094 Uiso 0.55 1 calc PR D 1
O1S O 0.4982(4) 0.7078(3) 0.6807(2) 0.0469(6) Uani 1 1 d D . .
H1SA H 0.547(5) 0.759(4) 0.637(3) 0.050 Uiso 1 1 d D . .
H1SB H 0.468(5) 0.752(4) 0.728(3) 0.050 Uiso 1 1 d D . .
O2S O 0.5363(6) 0.8936(5) 0.3094(3) 0.0986(16) Uani 1 1 d D . .
H2SA H 0.578(5) 0.969(2) 0.286(3) 0.050 Uiso 1 1 d D . .
H2SB H 0.631(4) 0.891(5) 0.291(4) 0.050 Uiso 1 1 d D . .
C9A C 0.7721(15) 0.3177(8) 0.9477(7) 0.052(3) Uani 0.45 1 d PDU B 2
H9A1 H 0.8658 0.3503 1.0057 0.063 Uiso 0.45 1 calc PR B 2
H9A2 H 0.6811 0.3381 0.9670 0.063 Uiso 0.45 1 calc PR B 2
C10A C 0.8244(14) 0.3734(11) 0.8517(9) 0.060(3) Uani 0.45 1 d PD B 2
H10D H 0.8642 0.4664 0.8660 0.091 Uiso 0.45 1 calc PR B 2
H10E H 0.7297 0.3393 0.7955 0.091 Uiso 0.45 1 calc PR B 2
H10F H 0.9123 0.3497 0.8331 0.091 Uiso 0.45 1 calc PR B 2
C19A C 0.2918(12) 0.3682(10) 0.7327(7) 0.051(3) Uani 0.45 1 d PDU D 2
H19C H 0.4133 0.4011 0.7435 0.061 Uiso 0.45 1 calc PR D 2
H19D H 0.2471 0.2753 0.7332 0.061 Uiso 0.45 1 calc PR D 2
C20A C 0.2364(12) 0.4373(10) 0.8154(7) 0.050(2) Uani 0.45 1 d PDU D 2
H20D H 0.2757 0.4220 0.8822 0.075 Uiso 0.45 1 calc PR D 2
H20E H 0.1161 0.4047 0.8025 0.075 Uiso 0.45 1 calc PR D 2
H20F H 0.2824 0.5289 0.8139 0.075 Uiso 0.45 1 calc PR D 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C7 89.76(18) . . ?
C11 S2 C17 90.41(15) . . ?
C1 N1 C2 113.2(3) . . ?
C1 N1 C8 123.2(3) . . ?
C2 N1 C8 123.5(3) . . ?
C11 N2 C12 112.9(3) . . ?
C11 N2 C18 122.8(3) . . ?
C12 N2 C18 124.3(3) . . ?
N1 C1 S1 114.6(3) . . ?
C7 C2 N1 111.8(3) . . ?
C7 C2 C3 121.2(3) . . ?
N1 C2 C3 127.0(3) . . ?
C4 C3 C2 117.0(4) . . ?
C3 C4 C5 121.9(3) . . ?
C6 C5 C4 121.2(4) . . ?
C5 C6 C7 117.2(4) . . ?
C2 C7 C6 121.5(3) . . ?
C2 C7 S1 110.7(3) . . ?
C6 C7 S1 127.8(3) . . ?
C9A C8 N1 117.5(5) . . ?
C9A C8 C9 25.1(4) . . ?
N1 C8 C9 109.6(4) . . ?
C10 C9 C8 118.2(8) . . ?
N2 C11 S2 114.6(2) . . ?
C17 C12 C13 121.6(3) . . ?
C17 C12 N2 111.6(3) . . ?
C13 C12 N2 126.8(3) . . ?
C14 C13 C12 116.8(3) . . ?
C13 C14 C15 122.0(3) . . ?
C16 C15 C14 120.9(3) . . ?
C15 C16 C17 117.7(3) . . ?
C16 C17 C12 121.1(3) . . ?
C16 C17 S2 128.5(3) . . ?
C12 C17 S2 110.5(2) . . ?
C19A C18 N2 120.7(5) . . ?
C19A C18 C19 25.2(4) . . ?
N2 C18 C19 108.2(4) . . ?
C20 C19 C18 117.9(7) . . ?
C8 C9A C10A 102.6(7) . . ?
C18 C19A C20A 105.0(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.683(4) . ?
S1 C7 1.747(3) . ?
S2 C11 1.678(3) . ?
S2 C17 1.739(3) . ?
N1 C1 1.317(4) . ?
N1 C2 1.392(4) . ?
N1 C8 1.479(5) . ?
N2 C11 1.325(4) . ?
N2 C12 1.397(4) . ?
N2 C18 1.473(4) . ?
C2 C7 1.374(5) . ?
C2 C3 1.400(4) . ?
C3 C4 1.376(5) . ?
C4 C5 1.387(6) . ?
C5 C6 1.378(5) . ?
C6 C7 1.395(5) . ?
C8 C9A 1.472(8) . ?
C8 C9 1.550(8) . ?
C9 C10 1.541(9) . ?
C12 C17 1.390(4) . ?
C12 C13 1.394(4) . ?
C13 C14 1.377(5) . ?
C14 C15 1.395(6) . ?
C15 C16 1.384(5) . ?
C16 C17 1.385(5) . ?
C18 C19A 1.448(8) . ?
C18 C19 1.556(8) . ?
C19 C20 1.529(8) . ?
C9A C10A 1.522(9) . ?
C19A C20A 1.515(9) . ?
